Water → Benzhydryl 2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetate

HRID 1906077Notes

Reaction equation

HRID 1906077 reaction equation
N(OC(C)(C)C)=O.[C:8]([O:12][C:13]([CH2:15][O:16][N:17]=[C:18]([C:35]1[N:36]=[C:37](N)[S:38][CH:39]=1)[C:19]([O:21][CH:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=[O:20])=[O:14])([CH3:11])([CH3:10])[CH3:9].C(OCC)(=O)C.O>O1CCCC1>[C:8]([O:12][C:13]([CH2:15][O:16][N:17]=[C:18]([C:35]1[N:36]=[CH:37][S:38][CH:39]=1)[C:19]([O:21][CH:22]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)=[O:20])=[O:14])([CH3:11])([CH3:9])[CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 10906Tert-Butyl nitriteHCID 53827226Benzhydryl 2-t-butoxycarbonylmethoxyimino-2-(2-aminothiazol-4-yl)acetate

Product 1

HCID 54223791Benzhydryl 2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetateYield 45.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of t-butyl nitrite (1.7 g) in tetrahydrofuran (10 ml) was dropwise added to a solution of benzhydryl 2-t-butoxycarbonylmethoxyimino-2-(2-aminothiazol-4-yl)acetate (syn isomer) (5 g) in tetrahydrofuran (50 ml) at 50° to 53° C. under stirring and the mixture was stirred at the same temperature at 25 minutes. The reaction mixture was poured into a mixture of ethyl acetate and water and the organic layer was separated. The organic layer was washed with brine and dried over magnesium sulfate. The solution was evaporated and the residue was subjected to column chlomatography on silica gel. The elution was carried out with a mixture of benzene and ethyl acetate (19:1) and the eluates containing the object compound were evaporated to give benzhydryl 2-t-butoxycarbonylmethoxyimino-2-(4-thiazolyl)acetate (syn isomer) (2.2 g).

Workup

  1. stirringthe mixture was stirred at the same temperature at 25 minutes
  2. customthe organic layer was separated
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solution was evaporated
  6. washThe elution
  7. additionwas carried out with a mixture of benzene and ethyl acetate (19:1)
  8. additionthe eluates containing the object compound
  9. customwere evaporated

Sources & evidence

ORD record
ord-0cad1c4028f74c0fbbe3bc7901a11a78
Source dataset
uspto-grants-1987_03
Patent number
US04649136

Reaction notes

Loading…